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Salidroside derivative and preparation method and application thereof

A compound and stereoisomer technology, applied in the field of salidroside derivatives and their preparation, can solve the problems of fast metabolism and low bioavailability, achieve broad application prospects, overcome low bioavailability, and excellent neuroprotection effect of action

Pending Publication Date: 2020-06-19
FUJIAN UNIV OF TRADITIONAL CHINESE MEDICINE
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Therefore, in order to overcome the shortcomings of low bioavailability and fast metabolism of salidroside in clinical application, appropriate modification of salidroside molecules to improve the lipid solubility of the molecules has become a research hotspot in the development of salidroside drugs

Method used

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  • Salidroside derivative and preparation method and application thereof
  • Salidroside derivative and preparation method and application thereof
  • Salidroside derivative and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] Embodiment 1, the preparation of salidroside derivative 1a of the present invention

[0041]

[0042] Add 3g (0.01mol) of salidroside sal, 1.06g (0.01mol) of sodium carbonate, 0.05g (0.155mmol) of tetrabutylammonium bromide, and 10ml of water into a 50ml three-necked flask. In an ice bath, stir until the solid is completely dissolved and the temperature of the system drops to -5°C to 5°C. Dissolve 0.01mol benzoyl chloride in 10ml ethyl acetate and add to the system. TLC (CHCl 3 :CH 3OH=4:1) monitor the reaction, and stop the reaction when the raw material point disappears. Ethyl acetate was added to the system after the reaction was completed, liquid separation was carried out, and extraction was performed 3 times, each time using 10 ml of ethyl acetate. The organic phases were combined, dried with anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to obtain a white solid. With silica gel as the stationary phase, (CHCl 3 -CH 3 OH) ...

Embodiment 2

[0043] Embodiment 2, the preparation of salidroside derivative 1b of the present invention

[0044]

[0045] With reference to the method of Example 1, benzoyl chloride was replaced by p-toluoyl chloride to obtain salidroside derivative 1b of the present invention: p-(p-toluyloxy)phenethyl-β-D -Glucopyranoside 2.4g, light yellow solid, yield 55%, the purity is 96% by peak area detected by HPLC, the molecular weight is determined by MS, and the structure is confirmed by combining NMR carbon spectrum and hydrogen spectrum. 1 HNMR(400MHz,MeOD)δ8.05(d,J=8.2Hz,2H),7.37(s,2H),7.35(t,J=2.0Hz,2H),7.21–7.03(m,2H),4.41– 4.28(m,1H),4.21–4.06(m,1H),3.90(dd,J=12.0,1.4Hz,1H),3.81(dt,J=9.7,7.2Hz,1H),3.75–3.66(m, 1H), 3.39(dd, J=12.8, 5.1Hz, 1H), 3.33(ddd, J=7.5, 5.7, 2.7Hz, 2H), 3.26–3.20(m, 1H), 3.07–2.88(m, 2H) ,2.43(d,J=17.2Hz,3H). 13 C NMR (101MHz, MeOD) δ165.47, 149.46, 144.66, 136.59, 129.73, 129.44, 129.09, 126.64, 121.24, 103.00, 76.72, 76.57, 73.72, 70.26, 70.14, 61.40, 35.30....

Embodiment 3

[0046] Embodiment 3, the preparation of salidroside derivative 1c of the present invention

[0047]

[0048] With reference to the method of Example 1, benzoyl chloride was replaced by p-ethylbenzoyl chloride to obtain salidroside derivative 1c of the present invention: p-(p-ethylbenzoyloxy)phenethyl-β-D -Glucopyranoside 0.9g, white solid, yield 42%, the purity was detected by HPLC, and the peak area was 95%, the molecular weight was determined by MS, and the structure was confirmed by combining NMR carbon spectrum and hydrogen spectrum. 1 HNMR(500MHz,MeOD)δ8.12–8.05(m,2H),7.39(d,J=8.4Hz,2H),7.36(d,J=8.5Hz,2H),7.16–7.09(m,2H), 4.35(d,J=7.8Hz,1H),4.19–4.10(m,1H),3.89(dt,J=9.5,4.9Hz,1H),3.81(dt,J=9.7,7.2Hz,1H),3.75 –3.66(m,1H),3.43–3.35(m,1H),3.33(ddd,J=7.9,6.4,4.5Hz,2H),3.23(dd,J=9.1,7.8Hz,1H),3.03–2.95 (m,2H),2.79–2.71(m,2H),1.29(t,J=7.6Hz,3H). 13 C NMR (126MHz, MeOD) δ165.47, 150.83, 149.48, 136.59, 129.86, 129.73, 127.93, 126.88, 121.24, 103.01, 76.73, 76.58, 73.73, 70...

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Abstract

The invention relates to a salidroside derivative and a preparation method and application thereof, and particularly provides a compound shown in a formula I, or salt thereof, or a stereoisomer thereof, or a crystal form thereof. The salidroside derivative shown in the formula I solves the problem of poor lipid solubility of salidroside, and can overcome the defects of low bioavailability and fastmetabolism of the salidroside in clinical application; and meanwhile, the salidroside derivative can effectively resist CoCl 2-induced PC12 cell apoptosis, has an excellent neuroprotective effect ona CoCl 2-induced PC12 cell hypoxia injury model, can be used for preparing drugs for preventing and / or treating various nervous system diseases (including parkinson disease, alzheimer disease, cerebral apoplexy and the like) related to cell hypoxia injury, and has broad application prospects.

Description

technical field [0001] The invention belongs to the technical field of medicine, and specifically relates to a salidroside derivative and its preparation method and application. Background technique [0002] Salidroside is the extract of Rhodiola rosea, a traditional Chinese medicine in my country, and it is also the main active ingredient of Rhodiola rosea and a marker of the substance basis of its efficacy. Many studies have shown that salidroside has anti-inflammatory, anti-oxidation, and anti-apoptotic effects, and has broad application prospects in the treatment of atherosclerosis and cardiovascular and cerebrovascular diseases. Literature "Salidroside on CoCl 2 Inducing the neuroprotective effect of hypoxic injury in PC12 cells" discloses the effect of salidroside on CoCl 2 The induced PC12 cell injury model has neuroprotective effect, which is related to inhibiting the complement component C3, promoting the expression of Egrs, further inhibiting the expression of Ba...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H15/18C07H1/00C07H1/06A61P25/00A61P25/16A61P25/28A61P9/10
CPCC07H15/18C07H1/00C07H1/06A61P25/00A61P25/16A61P25/28A61P9/10
Inventor 洪桂祝杨泽霖赖文芳褚克丹黄鑫
Owner FUJIAN UNIV OF TRADITIONAL CHINESE MEDICINE
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